With the exception of Craig Sager and Charles Barkley, few men have had the poise and confidence to make a pinstripe suit seem timeless.

From its popularization in the 1920’s and subsequently 1980’s Wall Street Culture, to its gradual decline by virtue of association with greed, subtler forms of this fine gentleman’s piece have made a strong revival in the modern man’s wardrobe, affording us yet another option to exercise as we continue to immerse ourselves in this intricate sartorial revolution.

The modern evolution of what was once a classic staple features an improved cut and shorter jacket length, affording the style a much more contemporary appeal. With modern, subtler stripes, the options for an attractive combination with the right shirt and suit is suddenly cast a much wider net.

Not bound by the chalk stripes of the 80’s that often left one looking more stuffy, the modern pinstripe has an air of lightness around it, that can make the discerning gentleman look both sophisticated and relaxed, all at once.

The modern version of the pinstripe suit features a more subtle pinstripe versus its classic counterpart of the 80′s

What type of Pinstripe Suit Should I pick?

Generally, the distance between the stripes on your suit will correlate to the amount of confidence you have when wearing a suit. If this is your first time delving in the world of pinstripe suits, narrower stripes would probably suit your wardrobe well.

If you are a pinstripe veteran, you could give your wardrobe a sartorial boost with a pinch of bravado by opting for a chalk stripe. Treat that choice with caution though!

As for your suit color, traditional colors of navy and charcoal grey will match up well with your shirts and ties. Regarding the stripe color, treat your preference for colors as you would the rest of your wardrobe.

For something more conservative, a light blue or navy stripe would work, whereas for a bolder look, pink and grey stripes on a navy suit could work. It ultimately emanates from your choice for colors.

Pinstripe Suit Combinations

Regarding suit combinations, while most men opt for a solid shirt with pinstripe suits so as to avoid pattern overload and confusion, with more experience, a checkered shirt and a contrasting patterned tie such as polka dots could work extremely well, providing that pattern sizes differ and that there is some contrast in color combinations between three layers in your suit! Mixing and matching three patterns requires a discerning eye. If pulled off correctly, you’ve created a head turner. Done wrong, however, and you’ll have heads being scratched. With three different patterns, you need to maintain so proportions and effect so that you don’t overdo congruency and you don’t exaggerate differences. There has to be a fine line, and it takes fine tuning to get there. Have fun with your sartorial pursuits!

With the right balance of pattern proportions and color, three patterns can work together seamlessly!

And that’s a wrap for this one. Have you embraced the Pinstripe Suit? We would love to see your comments below!

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Check out some of our favorite ties to match with your Pinstripe Suit(s) here at The Dark Knot!